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The title compound, C21H25NO2S, crystallizes in a centrosymmetric triclinic unit cell. In the mol­ecule, the bond lengths and angles are normal, and the di­hydro­pyrrole five-membered ring is almost planar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021342/cv6236sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021342/cv6236Isup2.hkl
Contains datablock I

CCDC reference: 226947

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.056
  • wR factor = 0.160
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Bruker, 2000); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 2000); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

3-Ethyl-1-(4-methylphenylsulfonyl)-4-phenethyl-4,5-dihydropyrrole top
Crystal data top
C21H25NO2SZ = 2
Mr = 355.48F(000) = 380
Triclinic, P1Dx = 1.248 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.250 (2) ÅCell parameters from 25 reflections
b = 10.740 (2) Åθ = 2.1–26.7°
c = 12.020 (2) ŵ = 0.19 mm1
α = 66.05 (3)°T = 293 K
β = 76.82 (3)°Needle, colourless
γ = 81.95 (3)°0.3 × 0.25 × 0.2 mm
V = 946.3 (4) Å3
Data collection top
Bruker P4
diffractometer
1852 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.041
Graphite monochromatorθmax = 25.0°, θmin = 1.9°
ω scansh = 09
Absorption correction: ψ scan
(SHELXTL; Bruker, 2000)
k = 1212
Tmin = 0.95, Tmax = 0.96l = 1314
3583 measured reflections3 standard reflections every 97 reflections
3330 independent reflections intensity decay: 0.001%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0753P)2 + 0.1421P]
where P = (Fo2 + 2Fc2)/3
3330 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.19 e Å3
6 restraintsΔρmin = 0.31 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.3639 (0.0105) x + 8.1775 (0.0118) y + 1.1362 (0.0189) z = 2.2885 (0.0084)

* -0.0196 (0.0019) N * 0.0216 (0.0020) C5 * -0.0133 (0.0021) C4 * 0.0113 (0.0020) C6 * 0.0000 (0.0020) C7

Rms deviation of fitted atoms = 0.0152

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.22026 (12)0.15212 (10)0.57309 (8)0.0649 (3)
O10.0880 (3)0.1860 (3)0.6575 (2)0.0912 (9)
O20.3332 (3)0.0372 (2)0.6176 (2)0.0758 (7)
N0.1331 (3)0.1237 (3)0.4785 (2)0.0556 (7)
C10.5920 (5)0.6519 (4)0.2235 (4)0.0956 (14)
H1B0.69470.62480.18060.143*
H1C0.61510.70600.26450.143*
H1D0.52160.70470.16520.143*
C20.3523 (6)0.0275 (5)0.1897 (4)0.1006 (15)
H2B0.38300.04320.11430.151*
H2C0.30340.10700.25550.151*
H2D0.44970.00870.21010.151*
C30.2315 (6)0.0892 (4)0.1730 (4)0.0871 (13)
H3A0.13550.06980.15000.105*
H3B0.28140.16790.10450.105*
C40.1723 (4)0.1258 (3)0.2831 (3)0.0565 (9)
C50.2296 (4)0.0781 (3)0.3869 (3)0.0557 (9)
H5A0.32440.02000.39930.067*
C60.0018 (4)0.2217 (3)0.4193 (3)0.0632 (10)
H6A0.01430.31190.41540.076*
H6B0.10810.19240.46610.076*
C70.0249 (4)0.2234 (3)0.2889 (3)0.0608 (9)
H7A0.07290.18540.28340.073*
C80.0468 (4)0.3654 (3)0.1850 (3)0.0613 (10)
H8A0.04420.35920.10720.074*
H8B0.04670.42560.20080.074*
C90.2082 (4)0.4287 (3)0.1716 (3)0.0551 (9)
H9A0.22380.41600.25320.066*
H9B0.30100.38100.13690.066*
C100.2108 (4)0.5776 (3)0.0911 (3)0.0477 (8)
C110.1152 (4)0.6721 (4)0.1314 (3)0.0616 (9)
H11A0.04970.64230.21050.074*
C120.1135 (5)0.8101 (4)0.0582 (4)0.0712 (10)
H12A0.04700.87200.08740.085*
C130.2118 (5)0.8549 (4)0.0589 (4)0.0696 (10)
H13A0.21230.94750.10910.084*
C140.3078 (4)0.7632 (3)0.1005 (3)0.0611 (9)
H14A0.37380.79340.17930.073*
C150.3083 (4)0.6262 (3)0.0270 (3)0.0533 (8)
H15A0.37510.56500.05690.064*
C210.3535 (5)0.5391 (4)0.3931 (4)0.0709 (11)
H21A0.30840.62530.38770.085*
C220.2686 (5)0.4253 (4)0.4756 (3)0.0650 (10)
H22A0.16670.43490.52470.078*
C230.3355 (4)0.2972 (3)0.4848 (3)0.0521 (8)
C240.4884 (4)0.2830 (3)0.4126 (3)0.0558 (9)
H24A0.53510.19690.41910.067*
C250.5701 (4)0.3983 (4)0.3312 (3)0.0635 (9)
H25A0.67310.38840.28350.076*
C260.5053 (5)0.5270 (4)0.3180 (3)0.0634 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0702 (6)0.0663 (6)0.0410 (5)0.0074 (5)0.0026 (4)0.0092 (4)
O10.095 (2)0.104 (2)0.0568 (15)0.0167 (16)0.0293 (15)0.0318 (15)
O20.0808 (14)0.0693 (13)0.0512 (12)0.0007 (11)0.0126 (11)0.0020 (10)
N0.0523 (16)0.0514 (16)0.0475 (16)0.0073 (13)0.0034 (14)0.0088 (14)
C10.096 (3)0.075 (3)0.102 (3)0.028 (2)0.009 (3)0.018 (2)
C20.097 (3)0.104 (4)0.109 (4)0.006 (3)0.007 (3)0.056 (3)
C30.110 (3)0.075 (3)0.085 (3)0.003 (3)0.029 (3)0.037 (2)
C40.062 (2)0.0447 (19)0.056 (2)0.0111 (17)0.0094 (18)0.0114 (17)
C50.055 (2)0.0406 (18)0.061 (2)0.0085 (15)0.0041 (18)0.0103 (17)
C60.0437 (19)0.053 (2)0.071 (2)0.0082 (16)0.0020 (17)0.0073 (18)
C70.053 (2)0.054 (2)0.068 (2)0.0153 (17)0.0142 (18)0.0109 (18)
C80.050 (2)0.055 (2)0.067 (2)0.0098 (16)0.0161 (18)0.0072 (18)
C90.0414 (18)0.0505 (19)0.057 (2)0.0058 (15)0.0067 (15)0.0049 (16)
C100.0392 (17)0.0516 (19)0.0459 (18)0.0049 (15)0.0081 (15)0.0115 (16)
C110.057 (2)0.066 (2)0.048 (2)0.0051 (18)0.0041 (17)0.0139 (18)
C120.074 (3)0.062 (2)0.072 (3)0.0069 (19)0.004 (2)0.028 (2)
C130.082 (3)0.047 (2)0.067 (2)0.007 (2)0.016 (2)0.0080 (19)
C140.063 (2)0.058 (2)0.0458 (19)0.0118 (18)0.0017 (17)0.0073 (18)
C150.0508 (19)0.057 (2)0.0463 (19)0.0037 (16)0.0038 (16)0.0168 (17)
C210.083 (3)0.060 (2)0.078 (3)0.001 (2)0.019 (2)0.034 (2)
C220.065 (2)0.072 (3)0.061 (2)0.003 (2)0.0008 (19)0.034 (2)
C230.054 (2)0.058 (2)0.0415 (17)0.0032 (16)0.0064 (16)0.0179 (16)
C240.051 (2)0.057 (2)0.054 (2)0.0002 (17)0.0117 (17)0.0169 (17)
C250.050 (2)0.072 (3)0.064 (2)0.0038 (19)0.0080 (18)0.023 (2)
C260.066 (2)0.064 (2)0.060 (2)0.016 (2)0.011 (2)0.0205 (19)
Geometric parameters (Å, º) top
S1—O11.427 (3)C8—H8A0.9700
S1—O21.431 (2)C8—H8B0.9700
S1—N1.618 (3)C9—C101.495 (4)
S1—C231.752 (3)C9—H9A0.9700
N—C51.419 (4)C9—H9B0.9700
N—C61.487 (4)C10—C111.374 (4)
C1—C261.504 (5)C10—C151.389 (4)
C1—H1B0.9600C11—C121.383 (4)
C1—H1C0.9600C11—H11A0.9300
C1—H1D0.9600C12—C131.382 (5)
C2—C31.463 (5)C12—H12A0.9300
C2—H2B0.9600C13—C141.359 (5)
C2—H2C0.9600C13—H13A0.9300
C2—H2D0.9600C14—C151.375 (4)
C3—C41.489 (5)C14—H14A0.9300
C3—H3A0.9700C15—H15A0.9300
C3—H3B0.9700C21—C221.381 (5)
C4—C51.313 (4)C21—C261.391 (5)
C4—C71.499 (5)C21—H21A0.9300
C5—H5A0.9300C22—C231.379 (4)
C6—C71.528 (5)C22—H22A0.9300
C6—H6A0.9700C23—C241.386 (4)
C6—H6B0.9700C24—C251.376 (5)
C7—C81.532 (4)C24—H24A0.9300
C7—H7A0.9800C25—C261.370 (5)
C8—C91.525 (4)C25—H25A0.9300
O1—S1—O2120.40 (16)C7—C8—H8A108.8
O1—S1—N106.26 (17)C9—C8—H8B108.8
O2—S1—N106.13 (15)C7—C8—H8B108.8
O1—S1—C23107.92 (17)H8A—C8—H8B107.6
O2—S1—C23108.73 (16)C10—C9—C8113.4 (3)
N—S1—C23106.61 (14)C10—C9—H9A108.9
C5—N—C6106.2 (3)C8—C9—H9A108.9
C5—N—S1120.9 (2)C10—C9—H9B108.9
C6—N—S1120.1 (2)C8—C9—H9B108.9
C26—C1—H1B109.5H9A—C9—H9B107.7
C26—C1—H1C109.5C11—C10—C15117.2 (3)
H1B—C1—H1C109.5C11—C10—C9120.9 (3)
C26—C1—H1D109.5C15—C10—C9121.8 (3)
H1B—C1—H1D109.5C10—C11—C12122.1 (3)
H1C—C1—H1D109.5C10—C11—H11A119.0
C3—C2—H2B109.5C12—C11—H11A119.0
C3—C2—H2C109.5C13—C12—C11119.1 (3)
H2B—C2—H2C109.5C13—C12—H12A120.4
C3—C2—H2D109.5C11—C12—H12A120.4
H2B—C2—H2D109.5C14—C13—C12119.7 (3)
H2C—C2—H2D109.5C14—C13—H13A120.1
C2—C3—C4115.5 (3)C12—C13—H13A120.1
C2—C3—H3A108.4C13—C14—C15120.6 (3)
C4—C3—H3A108.4C13—C14—H14A119.7
C2—C3—H3B108.4C15—C14—H14A119.7
C4—C3—H3B108.4C14—C15—C10121.1 (3)
H3A—C3—H3B107.5C14—C15—H15A119.4
C5—C4—C3128.1 (3)C10—C15—H15A119.4
C5—C4—C7110.5 (3)C22—C21—C26121.1 (3)
C3—C4—C7121.3 (3)C22—C21—H21A119.5
C4—C5—N113.7 (3)C26—C21—H21A119.5
C4—C5—H5A123.2C23—C22—C21119.7 (3)
N—C5—H5A123.2C23—C22—H22A120.1
N—C6—C7106.3 (3)C21—C22—H22A120.1
N—C6—H6A110.5C22—C23—C24120.0 (3)
C7—C6—H6A110.5C22—C23—S1121.0 (3)
N—C6—H6B110.5C24—C23—S1118.6 (3)
C7—C6—H6B110.5C25—C24—C23119.0 (3)
H6A—C6—H6B108.7C25—C24—H24A120.5
C4—C7—C6103.2 (3)C23—C24—H24A120.5
C4—C7—C8113.6 (3)C26—C25—C24122.4 (3)
C6—C7—C8114.3 (3)C26—C25—H25A118.8
C4—C7—H7A108.5C24—C25—H25A118.8
C6—C7—H7A108.5C25—C26—C21117.7 (3)
C8—C7—H7A108.5C25—C26—C1121.6 (4)
C9—C8—C7114.0 (3)C21—C26—C1120.6 (4)
C9—C8—H8A108.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11A···O1i0.932.863.472 (4)125
C12—H12A···O1i0.932.853.457 (5)124
C2—H2D···O2ii0.962.943.818 (5)153
C24—H24A···O2ii0.932.763.671 (4)167
C13—H13A···O2iii0.932.993.542 (5)120
C14—H14A···O2iii0.932.803.455 (4)128
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y, z+1; (iii) x, y+1, z1.
 

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